Synthesis, Antimicrobial Activity, Molecular Docking and DFT Study: Aryl‐Carbamic Acid 1‐Benzyl‐1H‐[1, 2, 3]Triazol‐4‐ylmethyl Esters. Issue 22 (12th June 2020)

• Record Type: Journal Article
• Authors: Naveen, ; Kumar Tittal, Ram; Vikas, Ghule D.; Rani, Poonam; Lal, Kashmiri; Kumar, Ashwani
• Is Part Of: ChemistrySelect. Volume 5:Issue 22(2020)
• Page Start: 6723
• Page End: 6729
• Publication Date: 2020-06-12
• Subjects: Antibiotic -- Antifungal agent -- Carbamate-linked- 1, 2, 3-triazole -- DFT study -- Molecular docking; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202001547
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Bioactive carbamate‐1, 4‐disubstituted 1, 2, 3‐triazole hybrid molecules were synthesized and characterized in high yield from carbamate‐linked terminal alkynes and in situ generated azides using Cell‐CuI‐NPs as heterogeneous catalysts via CuAAC reaction. The synthesized compound 8 demonstrated better antibacterial activity with MIC: 0.0077 μmol mL −1 for each bacterial strain E. coli, S. epidermidis and B. subtilis as compared to reference drug Norfloxacin (MIC: 0.0098 μmol mL −1 ). Also, the antifungal activity of compound 8 with MIC: 0.0077 μmol mL −1 for fungal strain C. albicans was found superior among all synthesized compounds and even better than reference drug Fluconazole with MIC: 0.0102 μmol mL −1 . The biological activity results were supported by molecular docking as well as DFT study. Abstract : A library of biologically active carbamate‐1, 4‐disubstituted‐1, 2, 3‐triazole hybrid molecules 4–18 were synthesized and fully characterized in good to excellent yield from carbamate‐linked terminal alkynes 2a‐c and in situ generated organic azides via CuAAC reaction using Cell‐CuI‐NPs as a heterogeneous catalyst in aqueous condition. Antimicrobial activity, molecular docking, Molinspiration bioactivity parameters for drug‐likeness and DFT studies were conducted on alkynes 2a‐c and carbamate‐1, 2, 3‐triazole compounds 4‐18 wherein results revealed that the incorporation of 1, 2, 3‐triazole ring improves the activity of the compounds.